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Cheap Flights from Chicago to Oakland $261.28

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Cheapest Flights from Chicago to Oakland (MDW to OAK)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Chicago to Oakland (MDW to OAK)

Question : Which airline can you expect delays with on this route?
Answer : Air Canada flights from MDW to OAK are delayed 100% of the time. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.

Question : What is the cheapest day to fly in the next four weeks?
Answer : Since low prices are preferred, look at January 31st. As of January 16th, the cheapest ticket sales are coming in 20% below the average price for this route, so you can spend that extra money on a fun experience in Oakland.

Question : Have you considered flying out of an airport besides Chicago Midway International Airport (MDW)?
Answer : Try searching for flights from O'Hare International Airport (ORD) as well. Over the next two months, flights from ORD to OAK are being booked 15% cheaper than flights from MDW to OAK. Being only 16 miles away, it's easily accessible for most.

Question : Do travelers from Chicago typically stay in Oakland for very long?
Answer : The average time spent in Oakland by travelers flying from MDW is eight days.

Question : Which airline is offering the cheapest round-trip flight from MDW to OAK?
Answer : Delta Air Lines is offering its passengers the cheapest flights over the next three months.